Leadership sector snapshot: Insurance

A look at the key leadership trends in insurance right now, and the critical skills required.

Insurance leaders are often promoted because of their technical expertise, sound judgement and ability to manage risk. These are the capabilities the industry depends on.

But stepping into leadership requires a fundamental shift. Success is no longer about having the best answer. It’s about creating the conditions for others to make good decisions, navigate ambiguity, build confidence and take ownership. It requires a transition not just in skill, but in identity.

This is where many new leaders find themselves caught. The behaviours that earned them credibility – being the expert, checking the detail, reducing risk and solving the problem – can become the very things that hold them back as leaders. Instead of enabling others, they unintentionally become the person everyone relies on.

The impact?

• Decision making slows
• Simple issues are escalated unnecessarily
• Senior leaders become bottlenecks
• Capable managers wait for permission instead of taking ownership

The insurance sector has built brilliant experts. Now it needs to build leaders who can convert expertise into judgement, pace and distributed ownership to take their businesses forward

The hidden cost of over-escalation

Most insurance organisations are not short of talent. They employ highly analytical, commercially astute individuals who are trained to think rigorously and minimise risk.

Through our work with large organisations across the sector, we’re seeing a consistent pattern. Many leaders are operating below the level their role requires. Decisions are escalated unnecessarily, senior leaders become bottlenecks, and ownership is deferred upwards rather than exercised where the capability already exists.

Over time, what begins as good risk management turns into organisational drag. The cost is rarely measured directly, but it is felt everywhere: in responsiveness, engagement, productivity and ultimately performance.

Why this is happening in insurance

Insurance is, by design, a high-control, highly regulated environment.

People are trained to gather evidence thoroughly, assess risk carefully and avoid error.

These are strengths – often non-negotiables – and have become traits that are part of a person’s identity (we’ll come on to talk more about that in a minute).

They also shape behaviour.

• A preference for certainty over action
• Escalating decisions rather than owning them
• Waiting for approval instead of moving with pace when urgency is required

Even at senior levels, many insurance organisations observe cultural tendencies towards caution and perfectionism that limit agility.

At the same time, leadership development is often inconsistent. Beyond technical and compliance requirements, many mid-level leaders receive little structured development, resulting in wide variation in leadership capability across the organisation.

The result is a workforce that is excellent at analysing risk, but less equipped for the realities of leadership today.

We regularly speak to L&D leaders across the insurance sector who need their leaders to navigate ambiguity with confidence, make sound judgements without perfect information, adapt at pace as circumstances change, and create confidence in others when there isn’t a single clear right answer.

The challenge isn’t a lack of capability. It’s helping exceptional experts make one of the most significant transitions of their career: from being valued for what they know to being valued for the judgement, confidence and ownership they create in others.

The leadership capability gap no one is talking about

Most leadership development will assess purely the skills these leaders need, which is obviously important – but there is a missing piece of the puzzle. (Here’s the identity bit we mentioned earlier.)

A gap that needs to be addressed is how leaders think about their role.

This transition – from expertise to judgement – is rarely made explicit, and even more rarely developed with the same intentionality as technical capability. Yet it is fundamental.

We ask delegates to consider “Who are you as a leader?” and “Why should anyone be led by you?” We explore what human capabilities they already bring, and where they can be improved. In practice, this means exploring:

• Personal narrative & values 
• Leadership identity and intention 
• Self-awareness under pressure 
• Default patterns 
• Personal impact on others 

“Of all the programmes we ran, this had the biggest impact in terms of promotions and results. The Ivy House programme is now by far the most successful and over-subscribed programme we run – and my proudest legacy.”

Global Talent Development Director, Aviva

Getting the right leadership development for insurance organisations

Even when organisations have already invested heavily in leadership development, behaviour often remains unchanged.

Why?

Because programmes typically focus on:

Building knowledge rather than changing behaviour: If leadership was simply about knowing what to do, bright, capable people could read a book or watch a video and become exceptional leaders. We know in reality, that doesn’t work. Leadership is about changing how people think, behave and respond under pressure – something that takes practice, feedback and reflection.

Developing individual capability without addressing the organisational environment:Traditional programmes focus on developing the individual, yet behaviour is heavily influenced by the organisational environment. Leaders are often expected to exercise judgement, empower others and take responsible risks, while the systems, culture and governance around them reinforce caution, escalation and dependency.

Treating leadership development as a learning event rather than a sustained journey: New habits take time to embed, particularly when leaders are challenging long-established ways of thinking and working. It takes sustained practice, real-world application and ongoing support for new behaviours to become habits that stick under pressure.

As a result, learning doesn’t deliver the impact organisations need. Leaders leave with some great models and concepts, but without the confidence, permission or organisational support to lead differently back in the business.

We take a different approach. In practice, this means focusing on five key areas.

1. From skills to identity

Ivy House leadership development focuses on how leaders see their role, not just what they do. Behaviour change follows identity change.

2. From theory to decision-making

The learning is embedded in real business scenarios, particularly those involving risk, trade-offs and incomplete information.

3. From certainty to ambiguity

We create space for leaders to practise decision-making without full data, not just in hindsight.

4. From empowerment rhetoric to clear guardrails

Empowerment only works when decision rights and boundaries are explicit.

5. From participation to measurable change

Success should be visible in:

• faster decision-making
• reduced escalation
• stronger accountability

Leading insurance organisations are increasingly explicit in expecting leadership programmes to demonstrate measurable behavioural change, strategic alignment and clear business impact.

Ivy House impact

68% increase in core leadership capabilities

42% promotion rate within 12 months

87% of line managers observed a positive performance impact

98% leave feeling more confident as leaders

The strategic opportunity for HR and L&D

This is about far more than developing better leaders. It’s about building an organisation that can make better decisions, respond faster to change and create leadership capacity at every level. When organisations successfully develop judgement-led leaders, they typically see:

• Faster, more confident decision-making
• Greater ownership and less unnecessary escalation
• Stronger succession pipelines.Better use of senior leadership capacity
• Increased organisational agility and resilience

This is why we’re seeing growing investment in this area. Leading organisations recognise that leadership capability is no longer just an L&D priority; it’s a strategic enabler of long-term performance.

Where to start

The organisations making the greatest progress don’t start by rolling out another leadership programme. They start by understanding the leadership challenge they’re trying to solve and creating the conditions for change.

A good place to begin is by asking:Where are decisions consistently delayed or unnecessarily escalated?Where does ownership sit higher in the organisation than it needs to?Is the barrier one of capability, opportunity or motivation?Where is confidence, rather than competence, limiting performance?Are our organisational systems reinforcing the behaviours we want, or working against them?Are senior leaders and directors creating the conditions for these behaviours to succeed through the way they lead, make decisions and respond to mistakes?Are all stakeholders aligned on the purpose of the development, the outcomes we’re looking for and how success will be measured?If we were to start small, who are our trailblazers? Which leaders are most open to learning, willing to role model new behaviours and able to create momentum for wider change?

Leadership development doesn’t happen in isolation. It succeeds when individual capability, leadership expectations and the organisational environment evolve together.

The organisations that will thrive in the next phase of the insurance market won’t simply be those with the strongest controls, processes or data. They will be those that build something much harder to replicate: leaders who exercise sound judgement, make confident decisions at pace and create the conditions for others to do the same..

So, do you have a plan to solve this leadership challenge? Speak to the Ivy House team to get started.